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Windward Software long-term review - the good and bad

⭐ Review Discussion 👁️ 2,791 views 💬 15 replies 📅 Oct 16, 2025
Hey everyone,

Windward Software long-term review - the good and bad

I'm running a grocery store in San Jose, CA and looking for advice. We currently have been looking at different options. Any recommendations or experiences to share?

Thanks in advance!
Amanda Scott 👑 Master
1,245 points • Member since Jun 2025

💬 15 Replies

Eric Coleman
👑 Master
219 posts
Oct 26, 2025
Different perspective here - you might want to consider a different approach
👍 Helpful (13) 🔗 Share
James Mitchell
👑 Master
221 posts
3w ago
This is why we switched to Thrive POS. No regrets.
👍 Helpful (4) 🔗 Share
Frances Russell
👑 Master
212 posts
3w ago
I've been using Auto-Star for 7 months and it has been working well for us
👍 Helpful (4) 🔗 Share
Nancy Sanders
👑 Master
217 posts
3w ago
Great question! In my experience with Clover Dining, it has been working well for us
👍 Helpful (0) 🔗 Share
Jerry Stewart
👑 Master
218 posts
3w ago
Check out the scale integration setting, that might help.
👍 Helpful (5) 🔗 Share
James Sanders
👑 Master
218 posts
2w ago
Agreed with the above. Also worth mentioning you should also check the settings
👍 Helpful (20) 🔗 Share
Carlos Hughes
👑 Master
235 posts
2w ago
Check out the produce lookup setting, that might help.
👍 Helpful (6) 🔗 Share
Nancy Rogers
👑 Master
225 posts
2w ago
Make sure you're on the latest version. That fixed it for us.
👍 Helpful (2) 🔗 Share
Karen Johnson
👑 Master
234 posts
2w ago
We had the same issue. What worked for us was restarting the terminal
👍 Helpful (2) 🔗 Share
David Wright
👑 Master
198 posts
1w ago
The WIC/EBT support is definitely worth the extra cost IMO.
👍 Helpful (20) 🔗 Share
Megan Foster
👑 Master
195 posts
1w ago
Had the same problem, support was very helpful when I contacted them.
👍 Helpful (6) 🔗 Share
Raymond Chen
👑 Master
191 posts
1w ago
Just went through this. Here's what I learned: take your time with the setup
👍 Helpful (12) 🔗 Share
Brenda Lewis
👑 Master
199 posts
1w ago
Cost us about $80/month all in. Worth it.
👍 Helpful (5) 🔗 Share
Frances Russell
👑 Master
212 posts
2d ago
Just went through this. Here's what I learned: take your time with the setup
👍 Helpful (2) 🔗 Share
Eugene Bennett
👑 Master
205 posts
2d ago
Check out the scale integration setting, that might help.
👍 Helpful (17) 🔗 Share

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